title: Synthesis of lipoic acid-peptide conjugates and their effect on collagen and melanogenesis.
abstract: We report new examples of lipoic acid (LA)-peptide conjugates, their potential as codrugs having anti-melanogenic and anti-aging properties was evaluated. These multifunctional molecules were prepared by linking lipophilic moiety (LA) to the pentapeptide KTTKS. The inhibitory effect of LA-peptide conjugates on melanin synthesis and tyrosinase activity is stronger than that of LA or the pentapeptide alone. Importantly, the conjugates display no cytotoxicity at a high concentration. LA-KTTKS and LA-PEG-KTTKS also inhibit UV-induced matrix metalloproteinase-1 expression up to 49.5% and 69.5% at 0.5 mM, respectively. LA-peptide conjugates stimulate collagen biosynthesis in fibroblasts more efficiently than their parent molecules do. These data suggest that LA-peptide conjugates may have cosmeceutical application as anti-melanogenic and anti-aging agents.
authors.affiliation: Department of Chemistry, School of Science, Beijing Technology and Business University, Beijing 100048, PR China. Electronic address: chichonglu@hotmail.com.
authors.forename: Chichong
authors.initials: C
authors.lastname: Lu
authors.forename: Bo Mi
authors.initials: BM
authors.lastname: Kim
authors.forename: Duckhee
authors.initials: D
authors.lastname: Lee
authors.forename: Min Hee
authors.initials: MH
authors.lastname: Lee
authors.forename: Jin Hwa
authors.initials: JH
authors.lastname: Kim
authors.forename: Hyeong-Bae
authors.initials: HB
authors.lastname: Pyo
authors.forename: Kyu Yun
authors.initials: KY
authors.lastname: Chai
mesh_terms: D000375:Aging / Q000187:drug effects; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D003094:Collagen / Q000096:biosynthesis*; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D017495:Hyperpigmentation / Q000188:drug therapy*; D020781:Matrix Metalloproteinase 1 / Q000096:biosynthesis / Q000378:metabolism; D008543:Melanins / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D009842:Oligopeptides / Q000737:chemistry*; D013329:Structure-Activity Relationship; D008063:Thioctic Acid / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D008543:Melanins; D009842:Oligopeptides; D008063:Thioctic Acid; D003094:Collagen; D020781:Matrix Metalloproteinase 1
keywords: Anti-melanogenic effects; Collagen; PEGylated lipoic acid ester; Peptide